63 Chesterfield Rd, Williamsburg, MA 01096
Siding in Chesterfield, Massachusetts
Compare contractors serving Chesterfield, Hampshire County — call them directly, or send one request and let qualified pros come to you.
50 contractors serving Chesterfield.
Contractors serving Chesterfield
- Guiel ConstructionServes Chesterfield · 4.4 mi★★★★★5.0 rating
- Sexton Roofing & SidingServes Chesterfield · 10.6 mi★★★★★4.8 rating
6 Church Ave, West Hatfield, MA 01088
- GL FOUR STAR HOME IMPROVEMENT INCServes Chesterfield · 11.0 mi★★★★★5.0 rating
80 Damon Rd # 1, Northampton, MA 01060
- Stone Mountain Roofing LLCServes Chesterfield · 11.1 mi★★★★★5.0 rating
156 Northampton St, Easthampton, MA 01027
- Dunn Rite Handyman Services LLCServes Chesterfield · 13.0 mi★★★★★4.8 rating
264 Long Plain Rd, South Deerfield, MA 01373
- Yeoman Design BuildServes Chesterfield · 14.5 mi★★★★★5.0 rating
123 Sandgully Rd N, South Deerfield, MA 01373
- Window Works, LLCServes Chesterfield · 14.6 mi★★★★★4.8 rating
321 Russell St, Hadley, MA 01035
- Northeastern Log HomesServes Chesterfield · 14.7 mi★★★★☆4.4 rating
1126 Southampton Rd, Westfield, MA 01085
- Chagnon Building & Remodeling, LLCServes Chesterfield · 14.9 mi★★★★★4.6 rating
91 Stockbridge St, Hadley, MA 01035
- Cameron Painting Inc / Established 1988Serves Chesterfield · 16.0 mi★★★★★4.5 rating
22 Whippletree Ln, Amherst, MA 01002
- Cowls Building SupplyServes Chesterfield · 16.1 mi★★★★★4.6 rating
125 Sunderland Rd, Amherst, MA 01059
- Hometown Metal RoofingServes Chesterfield · 16.1 mi★★★★★5.0 rating
627 Southampton Rd, Westfield, MA 01085
- JP Carroll RoofingServes Chesterfield · 16.2 mi★★★★★4.9 rating
20a Turnpike Industrial Rd, Westfield, MA 01085
- Morton Buildings, Inc.Serves Chesterfield · 16.2 mi★★★★★5.0 rating
563 Southampton Rd, Westfield, MA 01085
- NextGen RoofingServes Chesterfield · 16.3 mi★★★★★5.0 rating
549 Southampton Rd, Westfield, MA 01085
- Integrity Development & ConstructionServes Chesterfield · 16.6 mi★★★★★5.0 rating
110 Pulpit Hill Rd, Amherst, MA 01002
- Mayers Enterprise LLCServes Chesterfield · 16.6 mi★★★★★5.0 rating
427 Beech St, Holyoke, MA 01040
- Etinde PaintingServes Chesterfield · 16.6 mi★★★★☆3.7 rating
730 West St, Amherst, MA 01002
- The Axxion Company, LLCServes Chesterfield · 16.8 mi★★★★☆4.0 rating
67 Suffolk St, Holyoke, MA 01040
- Hawkins RoofingServes Chesterfield · 16.9 mi★★★★☆4.0 rating
15 Sunrise Ave, Deerfield, MA 01342
- Green CollarServes Chesterfield · 16.9 mi★★★★★4.9 rating
48 Lamb St, South Hadley, MA 01075
- Dicky Matos Roofing IncServes Chesterfield · 16.9 mi★★★★★4.8 rating
23 Hadley Mill Rd, Holyoke, MA 01040
- Serves Chesterfield · 17.5 mi
115 Market Hill Rd, Amherst, MA 01002
- Affordable Home RepairsServes Chesterfield · 17.7 mi★★★★★5.0 rating
88 Bemis St, Chicopee, MA 01013
- Cedar Falls ConstructionServes Chesterfield · 17.9 mi★★★★★5.0 rating
209 Prospect St, Chicopee, MA 01013
- 3D Home ImprovementsServes Chesterfield · 18.1 mi★★★★★5.0 rating
74 Old Holyoke Rd, Westfield, MA 01085
- Alliance Home Improvement IncServes Chesterfield · 18.1 mi★★★★★4.8 rating
375 Chicopee St, Chicopee, MA 01013
- Galvez Bros Painting LLCServes Chesterfield · 18.1 mi★★★★★5.0 rating
124 Laurel St, Greenfield, MA 01301
- Berkshire Home Pros, IncServes Chesterfield · 18.2 mi★★★★★4.7 rating
90 Flansburg Ave, Dalton, MA 01226
- d. hayward restorationServes Chesterfield · 18.5 mi★★★★★5.0 rating
111 River St, Greenfield, MA 01301
- Ideal Kitchens Home Improvement IncServes Chesterfield · 18.5 mi★★★★☆4.4 rating
838 Grattan St, Chicopee, MA 01020
- Eli PaintingServes Chesterfield · 18.7 mi★★★★★4.8 rating
199 Deerfield St, Greenfield, MA 01301
- N. Riley Construction, Inc.Serves Chesterfield · 18.9 mi★★★★☆4.1 rating
621 Grattan St, Chicopee, MA 01020
- BRJ BuildersServes Chesterfield · 19.0 mi★★★★★5.0 rating
30 Olive St, Greenfield, MA 01301
- Nova VC ConstructionServes Chesterfield · 19.0 mi★★★★★4.9 rating
591 Grattan St, Chicopee, MA 01020
- First Generation Construction LLCServes Chesterfield · 19.0 mi★★★★★4.7 rating
324 Main St, Greenfield, MA 01301
- Major Home Improvements LLC - RoofingServes Chesterfield · 19.1 mi★★★★★5.0 rating
22 Verona St, Westfield, MA 01085
- Keith G. Roy Construction, Inc.Serves Chesterfield · 19.2 mi★★★★☆4.3 rating
54 Mainline Dr, Westfield, MA 01085
- Yankee HomeServes Chesterfield · 19.5 mi★★★★★4.8 rating
36 Justin Dr, Chicopee, MA 01022
- Nucedar MillsServes Chesterfield · 19.7 mi★★★★☆4.3 rating
1000 Sheridan St, Chicopee, MA 01022
- Chamberland CedarServes Chesterfield · 19.9 mi★★★★★5.0 rating
14 Exchange St, Chicopee, MA 01013
- A-Z Exteriors, INCServes Chesterfield · 19.9 mi★★★★★5.0 rating
258 Hillside Rd, Southwick, MA 01077
- Homepro Handyman Services Inc. HomePro Of Pioneer ValleyServes Chesterfield · 20.1 mi★★★★★4.7 rating
178 Center St, Chicopee, MA 01013
- Fortini Construction and Remodeling INCServes Chesterfield · 20.2 mi★★★★★4.7 rating
138 Feeding Hills Rd, Westfield, MA 01085
- R & T Roofing and RemodelingServes Chesterfield · 20.4 mi★★★★★4.8 rating
30 Putnam Ave, Pittsfield, MA 01201
- Patrick Kelly Roofing & SidingServes Chesterfield · 20.4 mi★★★★★5.0 rating
12 Old Feeding Hills Rd, Westfield, MA 01085
- Serves Chesterfield · 20.5 mi
348 High St, Greenfield, MA 01301
- F&J Construction servicesServes Chesterfield · 20.6 mi★★★★★4.8 rating
63 Edward Ave, Pittsfield, MA 01201
- Lively Builders IncServes Chesterfield · 20.7 mi★★★★★4.9 rating
11 Hillside Rd, Montague, MA 01351
- A.R.K. BuildersServes Chesterfield · 20.7 mi★★★★★5.0 rating
32 Marlene Dr, Feeding Hills, MA 01030
Siding in Chesterfield — what to know
Energy & rebates
Chesterfield is served by National Grid, so homeowners are fully Mass Save eligible. The siding isn't rebated, but pulling the cladding is the cheapest window to insulate cavities, air-seal, and on the exposed upper sites and gorge-edge homes, add continuous exterior insulation.
Mass Save typically covers weatherization at 75% or more after a free Home Energy Assessment, and the 0% HEAT Loan can finance qualifying envelope work. The 1960s–80s ranches and contemporaries across Chesterfield were built to that era's loose insulation standards, and many older farmhouses have empty cavities. The rebated envelope work behind new siding is usually where the comfort and bill improvement come from.
Permits in Chesterfield
Chesterfield requires a building permit for residential re-siding through the town Building Department. The Westfield River corridor (a Wild & Scenic river), Chesterfield Gorge, and the network of tributary brooks put many parcels inside Wetlands Protection Act buffer zones, and Conservation Commission review is common; Wild & Scenic status can add review for ground-disturbing work along the river. With a 53-year median build, lead RRP applies to the older stock, and asbestos-cement shingle still turns up on mid-century homes.
Typical project cost
Re-siding a typical Chesterfield single-family runs roughly $10,000–$21,000 for vinyl, $12,500–$25,000 for insulated vinyl, and $16,500–$36,000 for fiber-cement. Cedar on the older farmhouses generally lands $20,000–$50,000 for a full wrap. Western Hampshire hilltown labor sits below the Northampton baseline. Chesterfield-specific drivers are gorge-edge access, long back-road driveways, and the higher fastener spec for the upper exposures.
About Chesterfield homes
Chesterfield is a Hampshire County hill town of about 996 residents across roughly 504 housing units, on the ridges west of Northampton above the Westfield River gorge. The town is largely forest, with Chesterfield Gorge and the Westfield River Wild & Scenic corridor defining the dramatic terrain on its eastern edge.
The median home is around 53 years old, with a stock that mixes 19th-century farmhouses along the original roads, 1960s–80s contemporaries and ranches on subdivided land, and newer custom builds on the back roads. Elevations across town range broadly, and gorge-edge sites add a real moisture and exposure profile that ordinary hill-town conditions don't quite capture.
Common questions — Siding in Chesterfield
- Does Mass Save cover insulation behind new siding in Chesterfield?
- Yes. Chesterfield is National Grid territory, so homeowners qualify for the full Mass Save program. The siding isn't rebated, but cavity insulation and air-sealing behind it are typically subsidized at 75%+ after a free Home Energy Assessment.
- I'm on a gorge-edge lot. Does that change the siding spec?
- Often yes. Gorge-side homes get more humidity, more freeze-thaw cycling, and more wind. Premium WRB, generous flashing details, and either fiber-cement or insulated vinyl tend to age better than basic vinyl on those exposures.
- Will a project near the Westfield River need Conservation review?
- Often yes. The river is Wild & Scenic, and many adjacent parcels sit inside Wetlands Protection Act buffer zones. Exterior work involving staging or grading can trigger review.
- Is asbestos siding common on Chesterfield homes?
- On the mid-century capes and ranches, yes — asbestos-cement shingle was widely used through the 1960s. A licensed inspector should sample any suspect material before demo.
- Do I need a permit to re-side in Chesterfield?
- Yes. The Chesterfield Building Department requires a permit, and a reputable contractor handles the paperwork and inspections.
